Best Life Insider

I'm an investor who gets hundreds of emails a day. Here's what I look for when deciding which emails to read -- or delete.

Ashlyn Gentry

  • Ashlyn Gentry is cofounder and managing partner of Attention Capital.
  • She is a media and tech investor who receives hundreds of cold emails.
  • The best way to get your message read is to email directly (don't LinkedIn message), give context to why the receiver needs to hear the information, and always read up on the company or person you're reaching out to.
  • Click here for more BI Prime stories.

As a media and tech investor, I get a ton of cold outreach. Which emails I decide to read, open, or delete is a process I've narrowed down to a science. You're busy, I'm busy, but there are things you can do to make your email worth the time it takes for me to read it, and possibly respond.

My holding company, Attention Capital, makes majority investments in media and tech companies and has brands like the Tribeca Film Festival and Girlboss in our portfolio. I hear from entrepreneurs every day looking for investment via email, LinkedIn messages, and even tweets.

Below are my three best tips for getting your email read, receiving a response, and possibly scheduling a meeting:

1. Email me directly, not on LinkedIn

It makes a big difference when someone takes the time to track down my work email as opposed to just sending a message on LinkedIn. It shows you took the time to find someone who knows someone who has my email. Not to mention, it's pretty easy to guess someone's company email these days. Send your email to a collection of BCC'd email addresses. You can bet that first.last@companyname is a good guess, and you can Google other common formats. That little bit of effort goes a long way--it indicates you give a damn enough to try harder than most others.

Bombarding me with generic LinkedIn messages that seem like copy and pastes you're sending to fifty others is a sure-fire way to make sure I don't respond. A caveat, though: please don't send email to my personal gmail. Many investors work hard to separate work from life where possible. It's good practice to respect that separation, and rely on your ability to find a work email.

2. Give me context

Why me? Of everyone you could have sent this email or deck to, why do you think I'm the right person to see it? What is it about my company and our investment thesis that makes you confident this email is something I'll think twice about? That's the answer I'm looking for in your email. Why are you reaching out to me and my company specifically?

And also, why you? Even if it's just a sentence, give me the most surface-level sense of who you are, and why we might work well together. If you want to stand out in a crowded inbox, think about what your unique value add is to a conversation. Both you and I meet interesting people every day -- what can you say to ensure I find you and your company interesting enough that I mention what you're working on to others at a cocktail hour? 

3. Do your homework

It's very clear when someone hasn't done any preparation prior to sending an email. This is critical. If you want to put yourself in a better position to have a successful email exchange or phone call with me, take even the simplest steps to find out about who I am and what I'm working on.

Read our website. Read articles that have been posted recently about what we're involved in. Read press releases about companies we've invested in. Know our history. Check my LinkedIn and ask an interesting question about me or my company that demonstrates you spent five minutes learning about what we do, in order to make sure what you do is a good fit. Oh, and while we're at it, spell my name right. Attention to detail matters.

SEE ALSO: My LinkedIn profile alone has landed me plenty of paid opportunities, including a $5,000 speaking gig — here's how I've optimized it to attract clients

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